KR20000069935A - 트리사이클릭 에리트로마이신 유도체 - Google Patents

트리사이클릭 에리트로마이신 유도체 Download PDF

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Publication number: KR20000069935A
Authority: KR; South Korea
Prior art keywords: hydrogen; compound; formula iii; methoxy; alkyl
Prior art date: 1997-01-07

Application number

KR1019997006148A

Other languages

English (en)

Korean (ko)

Inventor

오어얏선

팬리탐

츄다이엘티.

스피나케니쓰피.

핼러스로버트

엘리오트리차드엘.

투파노마이클

Original Assignee

스티븐 에프. 웨인스톡

아보트 러보러터리즈

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1997-01-07

Filing date

1997-04-07

Publication date

2000-11-25

1997-04-07 Application filed by 스티븐 에프. 웨인스톡, 아보트 러보러터리즈 filed Critical 스티븐 에프. 웨인스톡

2000-11-25 Publication of KR20000069935A publication Critical patent/KR20000069935A/ko

Links

ULGZDMOVFRHVEP-RWJQBGPGSA-N Erythromycin Chemical class O([C@@H]1[C@@H](C)C(=O)O[C@@H]([C@@]([C@H](O)[C@@H](C)C(=O)[C@H](C)C[C@@](C)(O)[C@H](O[C@H]2[C@@H]([C@H](C[C@@H](C)O2)N(C)C)O)[C@H]1C)(C)O)CC)[C@H]1C[C@@](C)(OC)[C@@H](O)[C@H](C)O1 ULGZDMOVFRHVEP-RWJQBGPGSA-N 0.000 title description 12
150000001875 compounds Chemical class 0.000 claims abstract description 852
238000000034 method Methods 0.000 claims abstract description 88
239000000203 mixture Substances 0.000 claims abstract description 74
239000008194 pharmaceutical composition Substances 0.000 claims abstract description 22
150000002148 esters Chemical class 0.000 claims abstract description 19
208000035143 Bacterial infection Diseases 0.000 claims abstract description 15
208000022362 bacterial infectious disease Diseases 0.000 claims abstract description 15
150000003839 salts Chemical class 0.000 claims abstract description 15
229910052739 hydrogen Inorganic materials 0.000 claims description 1092
239000001257 hydrogen Substances 0.000 claims description 1087
150000002431 hydrogen Chemical class 0.000 claims description 698
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 369
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 342
-1 hydrogen compound Chemical class 0.000 claims description 279
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 164
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical group ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 138
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 125
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 122
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 99
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 80
125000001072 heteroaryl group Chemical group 0.000 claims description 79
239000002904 solvent Substances 0.000 claims description 79
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 61
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 60
125000003118 aryl group Chemical group 0.000 claims description 60
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 57
238000006243 chemical reaction Methods 0.000 claims description 49
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 46
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 45
125000003107 substituted aryl group Chemical group 0.000 claims description 41
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 36
238000011282 treatment Methods 0.000 claims description 34
125000000592 heterocycloalkyl group Chemical group 0.000 claims description 32
125000001424 substituent group Chemical group 0.000 claims description 32
RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 claims description 28
239000000126 substance Substances 0.000 claims description 26
125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 23
239000000010 aprotic solvent Substances 0.000 claims description 22
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 21
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 20
239000002253 acid Substances 0.000 claims description 17
239000000460 chlorine Substances 0.000 claims description 17
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 claims description 17
SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 claims description 16
229910052757 nitrogen Inorganic materials 0.000 claims description 15
229910000104 sodium hydride Inorganic materials 0.000 claims description 15
125000000852 azido group Chemical group *N=[N+]=[N-] 0.000 claims description 14
PFKFTWBEEFSNDU-UHFFFAOYSA-N carbonyldiimidazole Chemical compound C1=CN=CN1C(=O)N1C=CN=C1 PFKFTWBEEFSNDU-UHFFFAOYSA-N 0.000 claims description 14
239000003937 drug carrier Substances 0.000 claims description 14
239000003960 organic solvent Substances 0.000 claims description 14
229910052794 bromium Inorganic materials 0.000 claims description 13
229910052801 chlorine Inorganic materials 0.000 claims description 13
FAMRKDQNMBBFBR-BQYQJAHWSA-N diethyl azodicarboxylate Substances CCOC(=O)\N=N\C(=O)OCC FAMRKDQNMBBFBR-BQYQJAHWSA-N 0.000 claims description 13
229910052731 fluorine Inorganic materials 0.000 claims description 13
125000005842 heteroatom Chemical group 0.000 claims description 13
229910052740 iodine Inorganic materials 0.000 claims description 13
239000003120 macrolide antibiotic agent Substances 0.000 claims description 13
241001465754 Metazoa Species 0.000 claims description 12
PXIPVTKHYLBLMZ-UHFFFAOYSA-N Sodium azide Chemical compound [Na+].[N-]=[N+]=[N-] PXIPVTKHYLBLMZ-UHFFFAOYSA-N 0.000 claims description 12
125000000217 alkyl group Chemical group 0.000 claims description 12
BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 claims description 12
230000002829 reductive effect Effects 0.000 claims description 12
WJKHJLXJJJATHN-UHFFFAOYSA-N triflic anhydride Chemical compound FC(F)(F)S(=O)(=O)OS(=O)(=O)C(F)(F)F WJKHJLXJJJATHN-UHFFFAOYSA-N 0.000 claims description 12
KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 claims description 11
241000124008 Mammalia Species 0.000 claims description 11
125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 11
229910052799 carbon Inorganic materials 0.000 claims description 11
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 11
125000004665 trialkylsilyl group Chemical group 0.000 claims description 11
229910052736 halogen Inorganic materials 0.000 claims description 10
150000002367 halogens Chemical class 0.000 claims description 10
239000003054 catalyst Substances 0.000 claims description 9
239000003153 chemical reaction reagent Substances 0.000 claims description 9
125000004433 nitrogen atom Chemical group N* 0.000 claims description 9
238000006751 Mitsunobu reaction Methods 0.000 claims description 8
239000002585 base Substances 0.000 claims description 8
125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims description 8
125000004429 atom Chemical group 0.000 claims description 7
BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 claims description 7
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical group [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 claims description 6
150000008064 anhydrides Chemical class 0.000 claims description 6
239000003638 chemical reducing agent Substances 0.000 claims description 6
125000006222 dimethylaminomethyl group Chemical group [H]C([H])([H])N(C([H])([H])[H])C([H])([H])* 0.000 claims description 6
FAMRKDQNMBBFBR-UHFFFAOYSA-N ethyl n-ethoxycarbonyliminocarbamate Chemical compound CCOC(=O)N=NC(=O)OCC FAMRKDQNMBBFBR-UHFFFAOYSA-N 0.000 claims description 6
150000004678 hydrides Chemical class 0.000 claims description 6
GUWHRJQTTVADPB-UHFFFAOYSA-N lithium azide Chemical compound [Li+].[N-]=[N+]=[N-] GUWHRJQTTVADPB-UHFFFAOYSA-N 0.000 claims description 6
229910000103 lithium hydride Inorganic materials 0.000 claims description 6
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 claims description 6
239000012279 sodium borohydride Substances 0.000 claims description 6
229910000033 sodium borohydride Inorganic materials 0.000 claims description 6
239000012312 sodium hydride Substances 0.000 claims description 6
ICBQNKQWOYQWLF-UHFFFAOYSA-N triphenylphosphane;hydrate Chemical group O.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 ICBQNKQWOYQWLF-UHFFFAOYSA-N 0.000 claims description 6
125000000524 functional group Chemical group 0.000 claims description 5
125000006483 4-iodobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1I)C([H])([H])* 0.000 claims description 4
238000010511 deprotection reaction Methods 0.000 claims description 4
238000004519 manufacturing process Methods 0.000 claims description 4
238000006798 ring closing metathesis reaction Methods 0.000 claims description 4
125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 claims description 3
229910000027 potassium carbonate Inorganic materials 0.000 claims description 3
125000006516 2-(benzyloxy)ethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])OC([H])([H])C([H])([H])* 0.000 claims description 2
125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 claims description 2
125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 2
125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 claims description 2
125000003143 4-hydroxybenzyl group Chemical group [H]C([*])([H])C1=C([H])C([H])=C(O[H])C([H])=C1[H] 0.000 claims description 2
BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 claims description 2
150000001260 acyclic compounds Chemical class 0.000 claims description 2
MKRTXPORKIRPDG-UHFFFAOYSA-N diphenylphosphoryl azide Chemical compound C=1C=CC=CC=1P(=O)(N=[N+]=[N-])C1=CC=CC=C1 MKRTXPORKIRPDG-UHFFFAOYSA-N 0.000 claims description 2
125000000896 monocarboxylic acid group Chemical group 0.000 claims description 2
229910052709 silver Inorganic materials 0.000 claims description 2
239000004332 silver Substances 0.000 claims description 2
230000002401 inhibitory effect Effects 0.000 claims 9
230000035484 reaction time Effects 0.000 claims 2
125000004391 aryl sulfonyl group Chemical group 0.000 claims 1
SIAPCJWMELPYOE-UHFFFAOYSA-N lithium hydride Chemical compound [LiH] SIAPCJWMELPYOE-UHFFFAOYSA-N 0.000 claims 1
238000002360 preparation method Methods 0.000 abstract description 10
230000000845 anti-microbial effect Effects 0.000 abstract description 7
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 93
239000000243 solution Substances 0.000 description 73
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 61
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 51
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 42
239000011541 reaction mixture Substances 0.000 description 41
235000019441 ethanol Nutrition 0.000 description 40
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 36
239000000741 silica gel Substances 0.000 description 34
229910002027 silica gel Inorganic materials 0.000 description 34
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 33
238000005481 NMR spectroscopy Methods 0.000 description 32
235000019439 ethyl acetate Nutrition 0.000 description 32
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 29
239000000543 intermediate Substances 0.000 description 28
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 27
238000010992 reflux Methods 0.000 description 26
239000000047 product Substances 0.000 description 25
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 24
239000012267 brine Substances 0.000 description 24
238000004587 chromatography analysis Methods 0.000 description 24
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 22
239000011734 sodium Substances 0.000 description 21
229960000583 acetic acid Drugs 0.000 description 17
229910000041 hydrogen chloride Inorganic materials 0.000 description 15
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 14
239000000463 material Substances 0.000 description 14
239000007858 starting material Substances 0.000 description 14
238000003786 synthesis reaction Methods 0.000 description 14
125000006239 protecting group Chemical group 0.000 description 13
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 12
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
125000006367 bivalent amino carbonyl group Chemical group [H]N([*:1])C([*:2])=O 0.000 description 12
STVVMTBJNDTZBF-UHFFFAOYSA-N -2-Amino-3-phenyl-1-propanol Natural products OCC(N)CC1=CC=CC=C1 STVVMTBJNDTZBF-UHFFFAOYSA-N 0.000 description 11
150000001412 amines Chemical class 0.000 description 10
239000000546 pharmaceutical excipient Substances 0.000 description 10
239000011780 sodium chloride Substances 0.000 description 10
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 9
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 9
WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 9
238000000746 purification Methods 0.000 description 9
238000003756 stirring Methods 0.000 description 9
GQHTUMJGOHRCHB-UHFFFAOYSA-N 2,3,4,6,7,8,9,10-octahydropyrimido[1,2-a]azepine Chemical compound C1CCCCN2CCCN=C21 GQHTUMJGOHRCHB-UHFFFAOYSA-N 0.000 description 8
GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 description 8
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical group N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
STVVMTBJNDTZBF-VIFPVBQESA-N L-phenylalaninol Chemical group OC[C@@H](N)CC1=CC=CC=C1 STVVMTBJNDTZBF-VIFPVBQESA-N 0.000 description 8
GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 8
229940126208 compound 22 Drugs 0.000 description 8
239000000284 extract Substances 0.000 description 8
239000008101 lactose Substances 0.000 description 8
VQSRKMNBWMHJKY-YTEVENLXSA-N n-[3-[(4ar,7as)-2-amino-6-(5-fluoropyrimidin-2-yl)-4,4a,5,7-tetrahydropyrrolo[3,4-d][1,3]thiazin-7a-yl]-4-fluorophenyl]-5-methoxypyrazine-2-carboxamide Chemical compound C1=NC(OC)=CN=C1C(=O)NC1=CC=C(F)C([C@@]23[C@@H](CN(C2)C=2N=CC(F)=CN=2)CSC(N)=N3)=C1 VQSRKMNBWMHJKY-YTEVENLXSA-N 0.000 description 8
239000003921 oil Substances 0.000 description 8
235000019198 oils Nutrition 0.000 description 8
229920006395 saturated elastomer Polymers 0.000 description 8
238000010561 standard procedure Methods 0.000 description 8
GHWVXCQZPNWFRO-ZXZARUISSA-N (2r,3s)-butane-2,3-diamine Chemical compound C[C@@H](N)[C@H](C)N GHWVXCQZPNWFRO-ZXZARUISSA-N 0.000 description 7
239000003814 drug Substances 0.000 description 7
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 7
WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 6
OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical compound N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 description 6
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 6
WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 6
DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 6
239000003795 chemical substances by application Substances 0.000 description 6
238000001816 cooling Methods 0.000 description 6
229940079593 drug Drugs 0.000 description 6
238000010438 heat treatment Methods 0.000 description 6
HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 6
229920001223 polyethylene glycol Polymers 0.000 description 6
239000000843 powder Substances 0.000 description 6
239000003826 tablet Substances 0.000 description 6
125000006559 (C1-C3) alkylamino group Chemical group 0.000 description 5
YSUIQYOGTINQIN-UZFYAQMZSA-N 2-amino-9-[(1S,6R,8R,9S,10R,15R,17R,18R)-8-(6-aminopurin-9-yl)-9,18-difluoro-3,12-dihydroxy-3,12-bis(sulfanylidene)-2,4,7,11,13,16-hexaoxa-3lambda5,12lambda5-diphosphatricyclo[13.2.1.06,10]octadecan-17-yl]-1H-purin-6-one Chemical compound NC1=NC2=C(N=CN2[C@@H]2O[C@@H]3COP(S)(=O)O[C@@H]4[C@@H](COP(S)(=O)O[C@@H]2[C@@H]3F)O[C@H]([C@H]4F)N2C=NC3=C2N=CN=C3N)C(=O)N1 YSUIQYOGTINQIN-UZFYAQMZSA-N 0.000 description 5
229910010082 LiAlH Inorganic materials 0.000 description 5
JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 5
229920002472 Starch Polymers 0.000 description 5
230000002411 adverse Effects 0.000 description 5
239000002775 capsule Substances 0.000 description 5
125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 description 5
238000000576 coating method Methods 0.000 description 5
239000002552 dosage form Substances 0.000 description 5
229960003276 erythromycin Drugs 0.000 description 5
125000004092 methylthiomethyl group Chemical group [H]C([H])([H])SC([H])([H])* 0.000 description 5
231100000252 nontoxic Toxicity 0.000 description 5
230000003000 nontoxic effect Effects 0.000 description 5
239000006187 pill Substances 0.000 description 5
125000006413 ring segment Chemical group 0.000 description 5
239000007909 solid dosage form Substances 0.000 description 5
235000019698 starch Nutrition 0.000 description 5
239000003039 volatile agent Substances 0.000 description 5
239000001993 wax Substances 0.000 description 5
PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 description 4
STVVMTBJNDTZBF-SECBINFHSA-N (2r)-2-amino-3-phenylpropan-1-ol Chemical compound OC[C@H](N)CC1=CC=CC=C1 STVVMTBJNDTZBF-SECBINFHSA-N 0.000 description 4
125000006700 (C1-C6) alkylthio group Chemical group 0.000 description 4
125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 description 4
OZAIFHULBGXAKX-VAWYXSNFSA-N AIBN Substances N#CC(C)(C)\N=N\C(C)(C)C#N OZAIFHULBGXAKX-VAWYXSNFSA-N 0.000 description 4
QMMFVYPAHWMCMS-UHFFFAOYSA-N Dimethyl sulfide Chemical class CSC QMMFVYPAHWMCMS-UHFFFAOYSA-N 0.000 description 4
239000012359 Methanesulfonyl chloride Substances 0.000 description 4
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 4
JRNVZBWKYDBUCA-UHFFFAOYSA-N N-chlorosuccinimide Chemical compound ClN1C(=O)CCC1=O JRNVZBWKYDBUCA-UHFFFAOYSA-N 0.000 description 4
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DCVICHWBECIALB-UHFFFAOYSA-N tert-butyl 2,3-dihydropyrrole-1-carboxylate Chemical compound CC(C)(C)OC(=O)N1CCC=C1 DCVICHWBECIALB-UHFFFAOYSA-N 0.000 description 1
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
QVPSOVQERIPRMD-UHFFFAOYSA-N tert-butyl n-(2,3-diaminopropyl)carbamate Chemical compound CC(C)(C)OC(=O)NCC(N)CN QVPSOVQERIPRMD-UHFFFAOYSA-N 0.000 description 1
JQCNNYTWXOUCDB-UHFFFAOYSA-N tert-butyl n-(2,3-diazidopropyl)carbamate Chemical compound CC(C)(C)OC(=O)NCC(N=[N+]=[N-])CN=[N+]=[N-] JQCNNYTWXOUCDB-UHFFFAOYSA-N 0.000 description 1
GTAVEQBEFSJELB-GFCCVEGCSA-N tert-butyl n-[(2r)-1-azido-3-phenylpropan-2-yl]carbamate Chemical compound CC(C)(C)OC(=O)N[C@@H](CN=[N+]=[N-])CC1=CC=CC=C1 GTAVEQBEFSJELB-GFCCVEGCSA-N 0.000 description 1
LDKDMDVMMCXTMO-GFCCVEGCSA-N tert-butyl n-[(2r)-1-hydroxy-3-phenylpropan-2-yl]carbamate Chemical compound CC(C)(C)OC(=O)N[C@@H](CO)CC1=CC=CC=C1 LDKDMDVMMCXTMO-GFCCVEGCSA-N 0.000 description 1
PYFXOUCQTPUBOG-UHFFFAOYSA-N tert-butyl n-[1,3-dihydroxy-2-(hydroxymethyl)propan-2-yl]carbamate Chemical compound CC(C)(C)OC(=O)NC(CO)(CO)CO PYFXOUCQTPUBOG-UHFFFAOYSA-N 0.000 description 1
IVFJORRHEURGIF-UHFFFAOYSA-N tert-butyl n-[3-(hydroxymethyl)oxetan-3-yl]carbamate Chemical compound CC(C)(C)OC(=O)NC1(CO)COC1 IVFJORRHEURGIF-UHFFFAOYSA-N 0.000 description 1
AWARHXCROCWEAK-UHFFFAOYSA-N tert-butyl n-prop-2-enylcarbamate Chemical compound CC(C)(C)OC(=O)NCC=C AWARHXCROCWEAK-UHFFFAOYSA-N 0.000 description 1
LPQZERIRKRYGGM-UHFFFAOYSA-N tert-butyl pyrrolidine-1-carboxylate Chemical compound CC(C)(C)OC(=O)N1CCCC1 LPQZERIRKRYGGM-UHFFFAOYSA-N 0.000 description 1
125000000037 tert-butyldiphenylsilyl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1[Si]([H])([*]C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
150000003512 tertiary amines Chemical class 0.000 description 1
FPGGTKZVZWFYPV-UHFFFAOYSA-M tetrabutylammonium fluoride Chemical compound [F-].CCCC[N+](CCCC)(CCCC)CCCC FPGGTKZVZWFYPV-UHFFFAOYSA-M 0.000 description 1
125000003718 tetrahydrofuranyl group Chemical group 0.000 description 1
BSYVTEYKTMYBMK-UHFFFAOYSA-N tetrahydrofurfuryl alcohol Chemical compound OCC1CCCO1 BSYVTEYKTMYBMK-UHFFFAOYSA-N 0.000 description 1
238000011285 therapeutic regimen Methods 0.000 description 1
125000001113 thiadiazolyl group Chemical group 0.000 description 1
AYEKOFBPNLCAJY-UHFFFAOYSA-O thiamine pyrophosphate Chemical compound CC1=C(CCOP(O)(=O)OP(O)(O)=O)SC=[N+]1CC1=CN=C(C)N=C1N AYEKOFBPNLCAJY-UHFFFAOYSA-O 0.000 description 1
125000001984 thiazolidinyl group Chemical group 0.000 description 1
125000000335 thiazolyl group Chemical group 0.000 description 1
125000001544 thienyl group Chemical group 0.000 description 1
125000005000 thioaryl group Chemical group 0.000 description 1
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
230000000699 topical effect Effects 0.000 description 1
231100000419 toxicity Toxicity 0.000 description 1
230000001988 toxicity Effects 0.000 description 1
239000000196 tragacanth Substances 0.000 description 1
235000010487 tragacanth Nutrition 0.000 description 1
229940116362 tragacanth Drugs 0.000 description 1
DBGVGMSCBYYSLD-UHFFFAOYSA-N tributylstannane Chemical compound CCCC[SnH](CCCC)CCCC DBGVGMSCBYYSLD-UHFFFAOYSA-N 0.000 description 1
125000006168 tricyclic group Chemical group 0.000 description 1
125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
ZDPHROOEEOARMN-UHFFFAOYSA-N undecanoic acid Chemical compound CCCCCCCCCCC(O)=O ZDPHROOEEOARMN-UHFFFAOYSA-N 0.000 description 1
229940070710 valerate Drugs 0.000 description 1
NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 description 1
235000019871 vegetable fat Nutrition 0.000 description 1
239000012991 xanthate Substances 0.000 description 1
239000011787 zinc oxide Substances 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H17/00—Compounds containing heterocyclic radicals directly attached to hetero atoms of saccharide radicals
- C07H17/04—Heterocyclic radicals containing only oxygen as ring hetero atoms
- C07H17/08—Hetero rings containing eight or more ring members, e.g. erythromycins
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/04—Antibacterial agents
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H17/00—Compounds containing heterocyclic radicals directly attached to hetero atoms of saccharide radicals

KR1019997006148A 1997-01-07 1997-04-07 트리사이클릭 에리트로마이신 유도체 KR20000069935A (ko)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US8/779,786		1997-01-07
US08/779,786 US6274715B1 (en)	1995-11-08	1997-01-07	Tricyclic erythromycin derivatives

Publications (1)

Publication Number	Publication Date
KR20000069935A true KR20000069935A (ko)	2000-11-25

Family

ID=25117567

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
KR1019997006148A KR20000069935A (ko)	1997-01-07	1997-04-07	트리사이클릭 에리트로마이신 유도체

Country Status (15)

Country	Link
US (1)	US6274715B1 (es)
EP (1)	EP0961776A1 (es)
JP (1)	JP2001507714A (es)
KR (1)	KR20000069935A (es)
CN (1)	CN1244202A (es)
AR (1)	AR006678A1 (es)
AU (1)	AU2449597A (es)
BR (1)	BR9714269A (es)
CA (1)	CA2277116A1 (es)
CZ (1)	CZ231599A3 (es)
HU (1)	HUP0001518A3 (es)
IL (1)	IL130328A0 (es)
NZ (1)	NZ336174A (es)
TW (1)	TW442490B (es)
WO (1)	WO1998030574A1 (es)

Families Citing this family (52)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
KR100523679B1 (ko) *	1996-09-04	2005-10-26	아보트 러보러터리즈	항균 활성을 지닌 6-ｏ-치환된 케톨라이드
FR2781484B1 (fr) *	1998-07-21	2001-08-10	Hoechst Marion Roussel Inc	Nouveaux derives de la 6-deoxy erythromycine, leur procede de preparation et leur application comme medicaments
FR2784682B1 (fr) *	1998-10-15	2002-12-06	Hoechst Marion Roussel Inc	Nouveaux derives 2-halogene de 5-0-desosaminylerythronolide a, leur procede de preparation et leur application comme medicaments
US6939861B2 (en)	1999-04-16	2005-09-06	Kosan Biosciences, Inc.	Amido macrolides
US6514944B2 (en)	1999-04-16	2003-02-04	Kosan Biosciences, Inc.	Macrolide antiinfective agents
US6451768B1 (en)	1999-04-16	2002-09-17	Kosan Biosciences, Inc.	Macrolide antiinfective agents
ATE340183T1 (de)	1999-04-16	2006-10-15	Kosan Biosciences Inc	Antiinfektiöse makrolidderivate
HUP0201516A3 (en) *	1999-05-24	2003-03-28	Pfizer Prod Inc	13-methyl-erythromycin derivatives, process for their preparation and pharmaceutical compositions containing them
US6569836B2 (en)	1999-12-02	2003-05-27	Abbott Laboratories	6-O-alkyl-2-nor-2-substituted ketolide derivatives
TWI290136B (en)	2000-04-05	2007-11-21	Daiichi Seiyaku Co	Ethylenediamine derivatives
EP1146051A3 (en) *	2000-04-10	2001-10-31	Pfizer Products Inc.	Erythromycin A derivatives
WO2003000680A1 (fr)	2001-06-20	2003-01-03	Daiichi Pharmaceutical Co., Ltd.	Derives de diamine
WO2003016302A1 (fr)	2001-08-09	2003-02-27	Daiichi Pharmaceutical Co., Ltd.	Derives de diamine
WO2003000657A1 (fr)	2001-06-20	2003-01-03	Daiichi Pharmaceutical Co., Ltd.	Derives de diamine
US20040014690A1 (en) *	2002-02-13	2004-01-22	Zhenkun Ma	Macrolides with activity against methicillin-resistant staphylococcus aureus
US7910558B2 (en) *	2002-05-13	2011-03-22	Enanta Pharmaceuticals, Inc.	Bridged macrocyclic compounds and processes for the preparation thereof
US6841664B2 (en) *	2002-07-25	2005-01-11	Enanra Pharmaceuticals, Inc.	6,11-4-carbon bridged ketolides
US7273853B2 (en) *	2002-05-13	2007-09-25	Enanta Pharmaceuticals, Inc.	6-11 bicyclic ketolide derivatives
AU2003234650A1 (en) *	2002-05-31	2003-12-19	Janssen Pharmaceutica N.V.	3-descladinosyl-6-o-carbamoyl and 6-o-carbonoyl macrolide antibacterial agents
US6750204B2 (en)	2002-06-25	2004-06-15	Enanta Pharmaceuticals, Inc.	11-C-substituted ketolides
US6812216B2 (en)	2002-06-25	2004-11-02	Enanta Pharmaceuticals, Inc.	11-C-substituted derivatives of clarithromycin
US7091196B2 (en) *	2002-09-26	2006-08-15	Rib-X Pharmaceuticals, Inc.	Bifunctional heterocyclic compounds and methods of making and using same
JP2006523229A (ja) *	2003-03-05	2006-10-12	リブ−エックスファーマシューティカルズ，インコーポレイテッド	二官能性複素環式化合物ならびにその製造および使用方法
EP1638549A4 (en)	2003-03-10	2011-06-15	Optimer Pharmaceuticals Inc	NEW ANTIBACTERIAL AGENTS
US20070149463A1 (en) *	2003-10-30	2007-06-28	Oyelere Adegboyega K	Bifunctional macrolide heterocyclic compounds and methods of making and using the same
EP1699808A1 (en) *	2003-11-18	2006-09-13	Rib-X Pharmaceuticals, Inc.	Bifunctional macrolide heterocyclic compounds and methods of making and using the same
AU2003304705A1 (en)	2003-12-24	2005-08-03	Enanta Pharmaceuticals, Inc.	11-csubsituted erythromycin derivatives
US7414030B2 (en) *	2004-01-07	2008-08-19	Enanta Pharmaceuticals, Inc.	6-11 Bicyclic erythromycin derivatives
WO2005070113A2 (en) *	2004-01-09	2005-08-04	Enanta Pharmaceuticals, Inc.	9n-substituted 6-11 bicyclic erythromycin derivatives
US7384921B2 (en) *	2004-02-20	2008-06-10	Enanta Pharmaceuticals, Inc.	Polymorphic forms of 6-11 bicyclic ketolide derivatives
EP1723159B1 (en)	2004-02-27	2019-06-12	Melinta Therapeutics, Inc.	Macrocyclic compounds and methods of making and using the same
TW200635600A (en) *	2004-12-13	2006-10-16	Enanta Pharm Inc	Tetracyclic bicyclolides
US7384922B2 (en) *	2005-05-04	2008-06-10	Enanta Pharmaceuticals, Inc.	6-11 bridged oxime erythromycin derivatives
US20060252710A1 (en) *	2005-05-04	2006-11-09	Guoqiang Wang	6-11 Bridged oxime erythromycin derivatives
CN101855219B (zh) *	2007-09-17	2014-06-25	英安塔制药有限公司	6，11-桥联的联芳大环内酯类
US8354383B2 (en) *	2007-09-17	2013-01-15	Enanta Pharmaceuticals, Inc.	6,11-bridged biaryl macrolides
US8273720B2 (en) *	2007-09-17	2012-09-25	Enanta Pharmaceuticals, Inc.	6,11-bicyclolides: bridged biaryl macrolide derivatives
EP2214484A4 (en) *	2007-10-25	2013-01-02	Cempra Pharmaceuticals Inc	PROCESS FOR PREPARING ANTIBACTERIAL MAKROLIDE AGENTS
US8208698B2 (en) *	2007-12-14	2012-06-26	Mela Sciences, Inc.	Characterizing a texture of an image
TW200946109A (en) *	2008-05-09	2009-11-16	Enanta Pharm Inc	Anti-bacterial activity of 9-hydroxy derivatives 6, 11-bicyclolides
US8796232B2 (en)	2008-10-24	2014-08-05	Cempra Pharmaceuticals, Inc.	Methods for treating resistant diseases using triazole containing macrolides
US9937194B1 (en)	2009-06-12	2018-04-10	Cempra Pharmaceuticals, Inc.	Compounds and methods for treating inflammatory diseases
AU2010292010B2 (en)	2009-09-10	2016-01-07	Cempra Pharmaceuticals, Inc.	Methods for treating malaria, tuberculosis and MAC diseases
US20110064287A1 (en) *	2009-09-14	2011-03-17	Alexandru Bogdan	Characterizing a texture of an image
CN104698749B (zh) *	2010-01-25	2019-11-19	罗门哈斯电子材料有限公司	包含含氮化合物的光致抗蚀剂
CN103080122A (zh)	2010-03-22	2013-05-01	森普拉制药公司	大环内脂的结晶形式及其用途
US9051346B2 (en)	2010-05-20	2015-06-09	Cempra Pharmaceuticals, Inc.	Process for preparing triazole-containing ketolide antibiotics
JP6042334B2 (ja)	2010-09-10	2016-12-14	センプラファーマシューティカルズ，インコーポレイテッド	疾患治療のための水素結合形成フルオロケトライド
CN104470527B (zh)	2012-03-27	2019-05-28	森普拉制药公司	用于施用大环内酯抗生素的肠胃外制剂
WO2014152326A1 (en)	2013-03-14	2014-09-25	Cempra Pharmaceuticals, Inc.	Methods for treating respiratory diseases and formulations therefor
US9751908B2 (en)	2013-03-15	2017-09-05	Cempra Pharmaceuticals, Inc.	Convergent processes for preparing macrolide antibacterial agents
CN104650166B (zh) *	2014-11-17	2017-12-05	广东东阳光药业有限公司	一种大环内酯的制备方法

Family Cites Families (5)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
KR0166096B1 (ko)	1990-11-28	1999-01-15	우에하라 아키라	6-0-메틸에리쓰로마이신 a 유도체
US5523399A (en)	1991-12-27	1996-06-04	Taisho Pharmaceutical Co., Ltd.	5-O-desosaminylerythronolide derivatives
ATE135707T1 (de)	1992-04-22	1996-04-15	Taisho Pharmaceutical Co Ltd	5-0-desosaminylerythronolid a derivate
JP3227871B2 (ja) *	1993-02-25	2001-11-12	大正製薬株式会社	６−ｏ−メチルエリスロマイシンａ誘導体
PT876388E (pt)	1995-11-08	2004-07-30	Abbott Lab	Derivados de eritromicina triciclica

1997
- 1997-01-07 US US08/779,786 patent/US6274715B1/en not_active Expired - Lifetime
- 1997-04-07 KR KR1019997006148A patent/KR20000069935A/ko not_active Application Discontinuation
- 1997-04-07 CZ CZ992315A patent/CZ231599A3/cs unknown
- 1997-04-07 JP JP53082898A patent/JP2001507714A/ja not_active Ceased
- 1997-04-07 EP EP97920261A patent/EP0961776A1/en not_active Withdrawn
- 1997-04-07 AU AU24495/97A patent/AU2449597A/en not_active Abandoned
- 1997-04-07 HU HU0001518A patent/HUP0001518A3/hu unknown
- 1997-04-07 NZ NZ336174A patent/NZ336174A/en unknown
- 1997-04-07 CA CA002277116A patent/CA2277116A1/en not_active Abandoned
- 1997-04-07 BR BR9714269-7A patent/BR9714269A/pt not_active IP Right Cessation
- 1997-04-07 IL IL13032897A patent/IL130328A0/xx unknown
- 1997-04-07 WO PCT/US1997/005871 patent/WO1998030574A1/en not_active Application Discontinuation
- 1997-04-07 CN CN97181288A patent/CN1244202A/zh active Pending
- 1997-04-14 TW TW086104775A patent/TW442490B/zh not_active IP Right Cessation
- 1997-04-16 AR ARP970101538A patent/AR006678A1/es unknown

Also Published As

Publication number	Publication date
CA2277116A1 (en)	1998-07-16
CN1244202A (zh)	2000-02-09
CZ231599A3 (cs)	1999-12-15
AU2449597A (en)	1998-08-03
HUP0001518A2 (hu)	2000-09-28
IL130328A0 (en)	2000-06-01
AR006678A1 (es)	1999-09-08
TW442490B (en)	2001-06-23
EP0961776A1 (en)	1999-12-08
US6274715B1 (en)	2001-08-14
JP2001507714A (ja)	2001-06-12
NZ336174A (en)	2001-02-23
BR9714269A (pt)	2000-04-18
HUP0001518A3 (en)	2001-11-28
WO1998030574A1 (en)	1998-07-16

Legal Events

Date	Code	Title	Description
2002-04-08	WITN	Application deemed withdrawn, e.g. because no request for examination was filed or no examination fee was paid

Publication	Publication Date	Title
KR20000069935A (ko)	2000-11-25	트리사이클릭 에리트로마이신 유도체
US6355620B1 (en)	2002-03-12	C-2 modified erythromycin derivatives
RU2601550C2 (ru)	2016-11-10	Кетолидные соединения
EP0876388B1 (en)	2004-02-18	Tricyclic erythromycin derivatives
US5780605A (en)	1998-07-14	6,9-bridged erythromycin derivatives
AU1286799A (en)	1999-05-17	6,11-bridged erythromycin derivatives
US4740502A (en)	1988-04-26	Semisynthetic erythromycin antibiotics
EP1206476B1 (en)	2006-01-04	9a-azalides with antibacterial activity
US6569836B2 (en)	2003-05-27	6-O-alkyl-2-nor-2-substituted ketolide derivatives
US6764996B1 (en)	2004-07-20	9a-azalides with antibacterial activity
CA2235942C (en)	2005-12-06	Tricyclic erythromycin derivatives
WO2001040241A2 (en)	2001-06-07	6-o-alkyl-2-nor-2-substituted ketolide derivatives
US20020193320A1 (en)	2002-12-19	C-2 modified erythromycin derivatives
EP1501847A2 (en)	2005-02-02	11-deoxy azalide antibacterials
EP1499326A1 (en)	2005-01-26	Oxolide antibacterials
MXPA00002977A (es)	2001-07-09	Fosfatos y fosfitos ciclicos